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Direct Enantioselective α-Allylation of Unfunctionalized Cyclic Ketones with Alkynes through Pd-Amine Cooperative Catalysis.

Byline: Jin Tu Danence Lee,Yu Zhao Keywords: cooperative catalysis; enamine catalysis; palladium pi-allyl; tertiary stereocenter; [alpha]-allylation of ketone Abstract The first direct enantioselective [alpha]-allylation of unfunctionalized cyclic ketones using alkynes as an economical choice of rea... Full description

Journal Title: Chemistry (Weinheim an der Bergstrasse Germany), July 5, 2018, Vol.24(38), pp.9520-9524
Main Author: Lee, Jin Tu Danence
Other Authors: Zhao, Yu
Format: Electronic Article Electronic Article
Language: English
Subjects:
ID: E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201802273
Link: http://search.proquest.com/docview/2036202650/?pq-origsite=primo
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title: Direct Enantioselective α-Allylation of Unfunctionalized Cyclic Ketones with Alkynes through Pd-Amine Cooperative Catalysis.
format: Article
creator:
  • Lee, Jin Tu Danence
  • Zhao, Yu
subjects:
  • Cooperative Catalysis
  • Enamine Catalysis
  • Palladium Pi-Allyl
  • Tertiary Stereocenter
  • Α-Allylation of Ketone
ispartof: Chemistry (Weinheim an der Bergstrasse, Germany), July 5, 2018, Vol.24(38), pp.9520-9524
description: Byline: Jin Tu Danence Lee,Yu Zhao Keywords: cooperative catalysis; enamine catalysis; palladium pi-allyl; tertiary stereocenter; [alpha]-allylation of ketone Abstract The first direct enantioselective [alpha]-allylation of unfunctionalized cyclic ketones using alkynes as an economical choice of reagent is reported. This transformation uses a simple procedure with commercially available palladium, chiral bisphosphine ligand and chiral amine catalysts, and affords valuable ketones with a [alpha]-tertiary stereocenter in good to high enantiopurity. In this transformation, a chiral palladium complex containing the (S)-DIFLUORPHOS ligand catalyzes the isomerization of alkynes into an electrophilic allylpalladium species, which is attacked by the enamine generated in situ from the condensation of (R)-prolinol with the ketone substrate. Supporting information: Additional Supporting Information may be found in the online version of this article As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. CAPTION(S): Supplementary
language: eng
source:
identifier: E-ISSN: 1521-3765 ; DOI: 10.1002/chem.201802273
fulltext: fulltext
issn:
  • 15213765
  • 1521-3765
url: Link


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titleDirect Enantioselective α-Allylation of Unfunctionalized Cyclic Ketones with Alkynes through Pd-Amine Cooperative Catalysis.
creatorLee, Jin Tu Danence ; Zhao, Yu
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ispartofChemistry (Weinheim an der Bergstrasse, Germany), July 5, 2018, Vol.24(38), pp.9520-9524
identifierE-ISSN: 1521-3765 ; DOI: 10.1002/chem.201802273
subjectCooperative Catalysis ; Enamine Catalysis ; Palladium Pi-Allyl ; Tertiary Stereocenter ; Α-Allylation of Ketone
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descriptionByline: Jin Tu Danence Lee,Yu Zhao Keywords: cooperative catalysis; enamine catalysis; palladium pi-allyl; tertiary stereocenter; [alpha]-allylation of ketone Abstract The first direct enantioselective [alpha]-allylation of unfunctionalized cyclic ketones using alkynes as an economical choice of reagent is reported. This transformation uses a simple procedure with commercially available palladium, chiral bisphosphine ligand and chiral amine catalysts, and affords valuable ketones with a [alpha]-tertiary stereocenter in good to high enantiopurity. In this transformation, a chiral palladium complex containing the (S)-DIFLUORPHOS ligand catalyzes the isomerization of alkynes into an electrophilic allylpalladium species, which is attacked by the enamine generated in situ from the condensation of (R)-prolinol with the ketone substrate. Supporting information: Additional Supporting Information may be found in the online version of this article As a service to our authors and readers, this journal provides supporting information supplied by the authors. Such materials are peer reviewed and may be re-organized for online delivery, but are not copy-edited or typeset. Technical support issues arising from supporting information (other than missing files) should be addressed to the authors. CAPTION(S): Supplementary
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